Herbicide combinations comprising L-glufosinate and indaziflam

ABSTRACT

The present invention primarily relates to specific herbicide combinations comprising (i) L-glufosinate and/or salts thereof and (ii) indaziflam and to compositions comprising said specific herbicide combinations. The present invention further relates to a method of producing said specific herbicide combinations and compositions comprising said specific herbicide combinations. The present invention also relates to the use of said specific herbicide combinations and compositions comprising said specific herbicide combinations in the field of agriculture, in particular as plant growth regulators and for controlling harmful plants or undesired plant growth, as well as to corresponding methods.

The present invention primarily relates to specific herbicidecombinations comprising (i) L-glufosinate and/or salts thereof and (ii)indaziflam and to compositions comprising said specific herbicidecombinations. The present invention further relates to a method ofproducing said specific herbicide combinations and compositionscomprising said specific herbicide combinations. The present inventionalso relates to the use of said specific herbicide combinations andcompositions comprising said specific herbicide combinations in thefield of agriculture, in particular as plant growth regulators and forcontrolling harmful plants or undesired plant growth, as well as tocorresponding methods.

U.S. Pat. No. 4,168,963 describes phosphorus-containing compounds withherbicidal activity, of which, in particular, phosphinothricin(2-amino-4-[hydroxy(methyl)phosphinoyl]butanoic acid; common name:glufosinate) and its salts have acquired commercial importance in theagrochemistry (agricultural chemistry) sector.

WO 00/16627 A1 teaches synergistic active substance combinations forcontrolling harmful plants, wherein as active substance (A) aminotriazines of a certain structure type are used.

WO 2004/069814 A1 describes amino-1,3,5 triazines N-substituted withchiral bicyclic radicals, and their use as herbicides and plant growthregulators.

WO 2006/007947 A1 discloses various herbicide combinations, comprisingconstituents (A) and (B), wherein as one possible constituent (A)indaziflam is mentioned, and as constituent (B) a large number of manydifferend other herbicides are listed.

WO 2010/009819 A2 relates to a method for selective weed control in turfor lawn by using compounds of formula (I) defined therein. In WO2010/009819 A2, indaziflam is one of the compounds of formula (I), andalso certain combinations of the compounds of formula (I) with furtherherbicides are disclosed in WO 2010/009819 A2.

Weed Technology 2013, 27, 422-429 reports on the burndown and weedcontrol to protect citrus plants by tank mixing saflufenacil,glufosinate and indaziflam.

CN 103 329 931 describes compositions of indaziflam and glufosinate in aratio of 1:(0.2 to 10).

The Horticultural Weed Control Report 2012 from the Oregon StateUniversity describes inter alia weed control in hazelnuts in LaneCounty, Oreg., where also mixtures of glufosinate and indaziflam wereused.

In their application, herbicidal crop protection agents (herbicides)known to date for controlling harmful plants or unwanted vegetation,e.g. in permanent crops or on permanent cropland, have somedisadvantages, be it (a) that they have no or else insufficientherbicidal activity against specific harmful plants, (b) that thespectrum of harmful plants which can be controlled with the herbicidesis not broad enough, (c) that the selectivity of herbicides in and thecompatibility with (young) plantation crops is too low, thereby causingunwanted damage and/or unwanted reduced harvest yields of the (young)plantation crops, (d) that the initial herbicidal activity is not highor not strong enough and/or (e) that the herbicidal activity does notlast long enough.

Overall, the herbicidal activity, i.e. one or more of the above aspects(a), (b) (c), (d) and/or (e) of the herbicides like (L-)glufosinateand/or agronomically acceptable salts thereof used so far still allowsome improvement.

Surprisingly, it has now been found that certain herbicide combinationsor compositions comprising said herbicide combinations exhibit thedesired herbicidal activity and are able to control harmful plants orunwanted vegetation in a more effective and more efficient manner.

The present invention primarily relates to a combination of herbicides(herbicide combination) comprising or consisting of

(i) L-glufosinate and/or agronomically acceptable salts thereof,and(ii) indaziflam,wherein the ratio by weight of the total amount of component (i) to thetotal amount of component (ii) ≥10:1, i.e. said ratio by weight is equalto or greater than 10:1.

Preferably, the ratio by weight of the total amount of component (i) tothe total amount of component (ii) in a herbicide combination accordingto the present invention is in the range of from 10:1 to 35:1.

More preferably, the ratio by weight of the total amount of component(i) to the total amount of component (ii) in a herbicide combinationaccording to the present invention is in the range of from 12:1 to 30:1,even more preferably in the range of from 15:1 to 25:1, and mostpreferably in the range of from 18:1 to 24:1.

Further, the present invention also relates to a composition comprisinga herbicide combination as defined hereinabove or hereinafter.

Thus, a composition according to the present invention comprises

(i) L-glufosinate and/or agronomically acceptable salts thereof,and(ii) indaziflam,wherein the ratio by weight of the total amount of component (i) to thetotal amount of component (ii) in said composition is ≥10:1, i.e. saidratio by weight is equal to or greater than 10:1, based on the totalweight of the composition.

Preferably, the ratio by weight of the total amount of component (i) tothe total amount of component (ii) in a composition according to thepresent invention is in the range of from 10:1 to 35:1, based on thetotal weight of the composition.

More preferably, the ratio by weight of the total amount of component(i) to the total amount of component (ii) in a composition according tothe present invention is in the range of from 12:1 to 30:1, even morepreferably in the range of from 15:1 to 25:1, and most preferably in therange of from 18:1 to 24:1, in each case based on the total weight ofthe composition.

The herbicide combinations and the compositions comprising saidherbicide combinations in accordance with the present invention exhibitan excellent herbicidal activity in controlling harmful plants orunwanted vegetation.

It has been found that the efficacy of L-glufosinate and/oragronomically acceptable salts thereof can be improved by combiningL-glufosinate and/or agronomically acceptable salts thereof withindaziflam in the ratio by weight as speficied in the context of thepresent invention.

The (use of a) herbicide combination according to the present inventionand the (use of a) composition comprising the herbicide combination asdefined in the context of the present invention show remarkablyhigher/stronger initial herbicidal activity (see above mentioned aspect(d)) than L-glufosinate and/or agronomically acceptable salts thereofalone.

The (use of a) herbicide combination according to the present inventionand the (use of a) composition comprising the herbicide combination asdefined in the context of the present invention show remarkably longerlasting herbicidal activity (see above mentioned aspect (e)) thanL-glufosinate and/or agronomically acceptable salts thereof alone. Forexample, said longer lasting herbicidal activity results in thesubstantial retardation or substantial suppression of regrowth of theharmful or undesired plants and/or substantial retardation orsubstantial suppression of germination of the harmful or undesiredplants.

The (use of a) herbicide combination according to the present inventionand the (use of a) composition comprising the herbicide combination asdefined in the context of the present invention is characterized by anoverall more rapidly commencing (i.e. earlier and faster) and a morelong-lasting herbicidal action, in comparison to L-glufosinate and/oragronomically acceptable salts thereof alone, when applied to harmful orundesired plants, parts of said harmful or undesired plants, or the areawhere the harmful or undesired plants grow, for example the area undercultivation, especially in post-emergence application.

Thus, indaziflam (component (ii) as defined in the context of thepresent invention) enhances, extends, and/or prolongs the herbicidalactivity of L-glufosinate and/or agronomically acceptable salts thereof(component (i) as defined in the context of the present invention).

The (use of a) herbicide combination according to the present inventionand the (use of a) composition comprising the herbicide combination asdefined in the context of the present invention also allow goodselectivity in and the compatibility with (young) plantation crops (seeabove mentioned aspect (c)), thereby avoiding or reducing unwanteddamage and/or unwanted reduced harvest yields of the (young) plantationcrops.

If a herbicide combination (used) according to the present invention orif a composition comprising the herbicide combination (used) in thecontext of the present invention is applied to the green parts of theharmful plants or undesired plants, growth likewise stops drastically avery short time after the treatment; typically, they die completelyafter a certain time, so that in this manner competition by the weeds,which is harmful to the (permanent) crops, is eliminated at a very earlypoint in time and in a sustained manner.

In addition, the (use of a) herbicide combination according to thepresent invention and the (use of a) composition comprising theherbicide combination as defined in the context of the present inventionallow very effective and efficient tree sucker control, and exhibit goodand improved rainfastness.

Further, the herbicide combinations (used) in accordance with thepresent invention and the compositions comprising said herbicidecombinations (used) in accordance with the present invention can beemployed as plant growth regulators.

The present invention further relates to a composition as defined hereinin the context of the present invention which additionally comprises oneor more further components selected from the group consisting offormulation auxiliaries, additives customary in crop protection, andfurther agrochemically active compounds (i.e. agrochemically activecompounds different from components (i) and (ii) as defined above, i.e.agrochemically active compounds other than (i) glufosinate and/oragronomically acceptable salts, L-glufosinate and agronomicallyacceptable salts thereof and (ii) indaziflam).

In a preferred embodiment, a combination of herbicides used in thecontext of the present invention and a composition as defined herein inthe context of the present invention is free of saflufenacil.

However, when a combination of herbicides used in the context of thepresent invention consists of herbicides (i) L-glufosinate and/oragronomically acceptable salts thereof and (ii) indaziflam, this meansthat in such a case the combination of herbicides used in the context ofthe present invention or the composition comprising said combination ofherbicides used in the context of the present invention does not containany further (i.e. no additional) herbicidal active ingredient, andpreferably does not contain any further agrochemically active compound.Such combinations of herbicides consisting of (i) L-glufosinate and/oragronomically acceptable salts thereof (L-glufosinate-ammonium beingpreferred) and (ii) indaziflam are particularly preferred in the contextof the present invention.

In this context, the term “further herbicidal active ingredient” and“further agrochemically active compound” refers to the herbicides andagrochemically active compounds (pesticides), respectively, listed in“The Pesticide Manual”, 16th edition, The British Crop ProtectionCouncil and the Royal Soc. of Chemistry, 2012 other than glufosinate andagronomically acceptable salts, L-glufosinate and agronomicallyacceptable salts thereof, and indaziflam.

In a preferred composition according to the present invention, the totalamount of component (i) is equal to or less than 600 g/L (g/L=gram perlitre), more preferably the total amount of component (i) is equal to orless than 450 g/L, and even more preferably the total amount ofcomponent (i) is equal to or less than 300 g/L, in each case based onthe total amount of the composition.

Preferably, the total amount of component (i) in a composition accordingto the present invention in the range of from 100 to 600 g/L, preferablyin the range of from 125 to 450 g/L, more preferably in the range offrom 125 to 300 g/L, even preferably in the range of from 125 to 250g/L, in each case based on the total amount of the composition.

In a preferred composition according to the present invention, the totalamount of component (ii) is in the range of from 2 to 20 g/L, preferablyin the range of from 3 to 15 g/L, more preferably in the range of from 3to 12 g/L, even preferably in the range of from 3 to 10 g/L, mostpreferably in the range of from 3 to 6 g/L, in each case based on thetotal amount of the composition.

Preferably, a composition according to the present invention is acomposition, wherein

the total amount of component (i) is in the range of from 125 to 300g/L, preferably in the range of from 125 to 250 g/L,andthe total amount of component (ii) is in the range of from 3 to 10 g/L,preferably in the range of from 3 to 6 g/L,in each case based on the total amount of the composition.

Thus, preferably, a composition according to the present invention is acomposition, wherein

the total amount of component (i) is in the range of from 125 to 300g/L,andthe total amount of component (ii) is in the range of from 3 to 10 g/L,in each case based on the total amount of the composition.

Also, preferably, a composition according to the present invention is acomposition, wherein

the total amount of component (i) is in the range of from 125 to 250g/L,andthe total amount of component (ii) is in the range of from 3 to 10 g/L,in each case based on the total amount of the composition.

Own experiments have shown that compositions according to the presentinvention comprising a total amount of component (i) in the range offrom 150 to 200 g/L, and a total amount of component (ii) in the rangeof from 4 to 6 g/L, in each case based on the total amount of thecomposition, are particularly suitable in the context of the presentinvention.

For example, a composition according to the present invention comprisinga total amount of component (i) of about 150 g/L, and a total amount ofcomponent (ii) of about 4 g/L, in each case based on the total amount ofthe composition, showed the advantages and effects described in thecontext of the present invention.

However, own experiments also showed that if the ratio of the totalamount of component (i) to the total amount of component (ii) in aherbicide combination according to the present invention is much greaterthan 35:1, e.g. 50:1 (i.e. ≥50:1), the beneficial effects observed inthe context of the present invention and mentioned above are notachieved to the desired extent anymore.

Therefore, the ratio by weight of the total amount of component (i) tothe total amount of component (ii) in a herbicide combination accordingto the present invention preferably is in the range of from 10:1 to35:1, more preferably in the preferred ranges mentioned above.

The present invention preferably relates to the use of a combination ofherbicides or to the use of a composition comprising a combination ofherbicides as defined in the context of the present invention, in or onpermanent cropland, or on permanent crops.

A permanent crop is one produced from plants which last for manyseasons, rather than being replanted after each harvest. Permanent cropsare grown on permanent crop land in the form of agricultural land thatincludes grasslands and shrublands, e.g. used to grow grape vines orcoffee; orchards used to grow fruit or olives; and forested plantations,e.g. used to grow nuts or rubber. It does not include, however, treefarms intended to be used for wood or timber.

Preferred permanent croplands in the context of the present inventionare plantations, grasslands and shrublands. Preferably, the permanentcrops in the context of the present invention are plantation crops, andpreferably are selected from the group consisting fruit crops andorchard crops (preferably fruit trees, citrus trees, mango trees, olivetrees, grape vines, coffee, cocoa, tea, and berries (such asstrawberries, raspberries, blueberries and currants)), Musaceae sp.crops (for example banana or plantain crops), nut trees (preferablyalmond trees, walnut trees, pistachio trees, pecan trees, hazelnuttrees), oil palm trees, rubber trees, sugarcane and cotton.

More preferably, the permanent crops in the context of the presentinvention are fruit trees (preferably pome fruit trees and stone fruittrees; preferred fruit trees are apple trees, pear trees, apricot trees,plum trees, cherry trees, peach trees), olive trees, grape vines,coffee, tea), Musaceae sp. crops (preferably banana crops or plantaincrops), nut trees (preferably almond trees, walnut trees, pistachiotrees, pecan trees, hazelnut trees), oil palm trees, rubber trees, andcitrus crops (preferably lemon, orange or grapefruit crops).

Even more preferably, the permanent crops in the context of the presentinvention are selected from the group consisting of apple trees, peartrees, apricot trees, plum trees, cherry trees, peach trees, olivetrees, grape vines, coffee, tea, banana crops, nut trees (preferablyalmond trees, walnut trees, pistachio trees), oil palm trees, rubbertrees, and citrus crops (preferably lemon, orange or grapefruit crops).

Particularly preferably, the permanent crops in the context of thepresent invention are selected from the group consisting of apple trees,pear trees, apricot trees, plum trees, cherry trees, peach trees, olivetrees, grape vines, coffee, tea, banana crops, almond trees, walnuttrees, oil palm trees, rubber trees, lemon crops, orange crops andgrapefruit crops.

The herbicides used in the context of the present invention are knownper se, and described inter alia in “The Pesticide Manual”, 16thedition, The British Crop Protection Council and the Royal Soc. ofChemistry, 2012 and the literature cited therein. The herbicides used inthe context of the present invention are described in more detailhereinbelow.

According to the present invention the expression “composition” includescompositions comprising a herbicide combination as defined herein, andcan be used in various acceptable or agronomically typical forms andformulations, for example in a single “ready-mix” form.

The herbicides (i) and (ii) used in the herbicide combinations used inthe context of the present invention and the compositions comprising theherbicide combinations used in the context of the present invention maybe a combined spray mixture composed from separate formulations of thesingle active compounds, such as a “tank-mix”, or said composition canbe a combined use of the single active ingredients when applied in asequential manner, i.e. one after the other within a reasonably shortperiod, such as a few hours (and preferably less than 24 hours).

The salts of compounds used in the context of the present invention maybe used in the form of the respective agronomically acceptable salts,such as alkali metal salts, alkaline earth salts or ammonium salts.

Component (i) of a herbicide combination according to the presentinvention is L-glufosinate and/or agronomically acceptable saltsthereof.

Glufosinate (IUPAC-Name:(2RS)-2-amino-4-[hydroxy(methyl)phosphinoyl]butyric acid or4-[hydroxy(methyl)phosphinoyl]-DL-homoalanine, CAS Reg. No. 51276-47-2)and agronomically acceptable salts thereof are known, in particularglufosinate-ammonium (IUPAC-Name: ammonium(2RS)-2-amino-4-(methylphosphinato)butyric acid, CAS Reg. No.77182-82-2).

Glufosinate is represented by the following structure (1):

The compound of formula (1) is a racemate.

In the context of the present invention, the term “L-glufosinate” onlyrelates to the L-enantiomer of glufosinate.

Preferably, the agronomically acceptable salts of L-glufosinate are thesodium, potassium or ammonium (NH₄ ⁺) salts of L-glufosinate, inparticular glufosinate-P-ammonium and glufosinate-P-sodium, i.e.glufosinate-P-ammonium (IUPAC-Name: ammonium(2S)-2-amino-4-(methylphosphinato)butyric acid, CAS Reg. No.73777-50-1), and glufosinate-P-sodium (IUPAC-Name: sodium(2S)-2-amino-4-(methylphosphinato)butyric acid; CAS Reg. No.70033-13-5).

L-glufosinate can be obtained commercially, or may be prepared forexample as described in EP0248357A2, EP0249188A2, EP0344683A2,EP0367145A2, or EP0477902A2.

Component (ii) of a herbicide combination according to the presentinvention is indaziflam (IUPAC-Name:N²-[(1R,2S)-2,3-dihydro-2,6-dimethyl-1H-inden-1-yl]-6-[(1RS)-1-fluoroethyl]-1,3,5-triazine-2,4-diamine,CAS Reg. No. 950782-86-2, its (1*R)-1-fluoroethyl diastereoisomer, CASReg. No. 730979-19-8, and its (1*S)-1-fluoroethyl diastereoisomer CASReg. No. 730979-32-5) are known and described for example in WO2004/069814 A1 and U.S. Pat. No. 6,069,114 A.

In the context of the present invention, component (ii) preferablyrefers to indaziflam, wherein the ratio by weight of the total amount ofthe (1*R)-1-fluoroethyl diastereoisomer of indaziflam is equal to orgreater than the total amount of the (1*S)-1-fluoroethyl diastereoisomerof indaziflam, more preferably said ratio is greater than 2:1, morepreferably greater than 3:1, even more preferably greater than 5:1, andparticularly preferably greater than 10:1.

Most preferably in the context of the present invention, component (ii)only refers to the (1*R)-1-fluoroethyl diastereoisomer of indaziflam(CAS Reg. No. 730979-19-8), represented by the following structure (the(1*R)-1-fluoroethyl moiety is marked with an asterisk 1*R):

In accordance with the present invention, the herbicide combinations asdefined herein or the composition comprising a herbicide combination asdefined herein comprise a herbicidally effective amount of saidherbicide combination and may comprise further components, for exampleagrochemically active compounds of a different type and/or formulationauxiliaries and/or additives customary in crop protection, or they maybe employed together with these.

In accordance with the present invention, the herbicide combinations asdefined herein or the composition comprising a herbicide combination asdefined herein may be applied as a split application over time. Anotherpossibility is the application of the individual herbicides (i) and (ii)or the herbicide combinations in a plurality of portions (sequentialapplication).

Preferred is the simultaneous or nearly simultaneous application of theherbicides (i) and (ii) as defined herein. In the latter context, anearly simultaneous application of the herbicides (i) and (ii) asdefined herein means that the herbicide (i) L-glufosinate and/oragronomically acceptable salts thereof and the herbicide (ii) indaziflamare applied within 24 hours, preferably within 12 hours, more preferablywithin 6 hours, even more preferably within 3 hours.

In a particularly preferred embodiment, the herbicides (i) and (ii) asdefined herein are used together, i.e. at the same time. Thus, in aparticularly preferred embodiment, the compositions as defined in thecontext of the present invention are used.

The effects observed when using the herbicide combinations as definedaccording to the present invention or the compositions according to thepresent invention allow a more potent herbicidal action (in particular ahigher/stronger initial herbicidal activity), an extended herbicidalactivity period and/or a reduced number of required individualapplications and—as a result—more advantageous weed control systems bothfrom an economical and ecological point of view.

In a preferred embodiment, the herbicide combination (used) inaccordance with the present invention or the composition comprising theherbicides (i) and (ii) (used) in accordance with the present inventionis applied once, twice or three times per Gregorian calendar year, i.e.in one application, in two applications or in three applications peryear according to the Gregorian calendar.

In a preferred embodiment, the herbicide combination (used) inaccordance with the present invention or the composition comprising theherbicides (i) and (ii) (used) in accordance with the present inventionis applied twice time per Gregorian calendar year, i.e. in twoapplications per year according to the Gregorian calendar.

In an alternatively preferred embodiment, the herbicide combination(used) in accordance with the present invention or the compositioncomprising the herbicides (i) and (ii) (used) in accordance with thepresent invention is applied one time per Gregorian calendar year, i.e.in one application per year according to the Gregorian calendar.

In a preferred embodiment, the herbicide combination (used) inaccordance with the present invention or the composition comprising theherbicides (i) and (ii) (used) in accordance with the present inventionis applied one time in about 12 months, i.e. in one application in about12 months.

The herbicide combinations according to the present invention and thecompositions comprising the herbicides (i) and (ii) as defined in thecontext of the present invention are preferably used in post-emergenceapplications.

Furthermore, the herbicides (i) and (ii) as defined herein can be usedtogether with other agrochemically active compounds, for example fromthe group of the safeners, fungicides, insecticides, other herbicidesand other plant growth regulators, or with formulation auxiliaries andadditives customary in crop protection. Additives are, for example,fertilizers and colorants.

The combination of herbicides as defined in the context of the presentinvention or the composition according to the present invention have anoutstanding herbicidal activity against a broad spectrum of economicallyimportant harmful monocotyledonous and dicotyledonous harmful plants.Also here, post-emergence application is preferred.

Specifically, examples may be mentioned of some representatives of themonocotyledonous and dicotyledonous weed flora which can be controlledby the combinations according to the invention, without the enumerationbeing a restriction to certain species.

In the context of the present text, reference may be made to growthstages according to the BBCH monograph “Growth stages of mono- anddicotyledonous plants”, 2^(nd) edition, 2001, ed. Uwe Meier, FederalBiological Research Centre for Agriculture and Forestry (BiologischeBundesanstalt für Land and Forstwirtschaft).

Examples of monocotyledonous harmful plants on which the herbicidalcombinations and compositions according to the present invention actefficiently are from amongst the genera Hordeum spp., Echinochloa spp.,Poa spp., Bromus spp., Digitaria spp., Eriochloa spp., Setaria spp.,Pennisetum spp., Eleusine spp., Eragrostis spp., Panicum spp., Loliumspp., Brachiaria spp., Leptochloa spp., Avena spp., Cyperus spp.,Axonopris spp., Sorghum spp., and Melinus spp.

Particular examples of monocotyledonous harmful plants species on whichthe herbicidal combinations and compositions according to the presentinvention act efficiently are selected from from amongst the speciesHordeum murinum, Echinochloa crus-galli, Poa annua, Bromus rubens L.,Bromus rigidus, Bromus secalinus L., Digitaria sanguinalis, Eriochloagracilis, Setaria faberi, Setaria viridis, Pennisetum glaucum, Eleusineindica, Eragrostis pectinacea, Panicum miliaceum, Lolium multiflorum,Brachiaria platyphylla, Leptochloa fusca, Avena fatua, Cyperuscompressus, Cyperus esculentes, Axonopris offinis, Sorghum halapense,and Melinus repens.

Examples of dicotyledonous harmful plants on which the herbicidalcombinations and compositions according to the present invention actefficiently are from amongst the genera Amaranthus spp., Polygonum spp.,Medicago spp., Mollugo spp., Cyclospermum spp., Stellaria spp.,Gnaphalium spp., Taraxacum spp., Oenothera spp., Amsinckia spp., Erodiumspp., Erigeron spp., Senecio spp., Lamium spp., Kochia spp., Chenopodiumspp., Lactuca spp., Malva spp., Ipomoea spp., Brassica spp., Sinapisspp., Urtica spp., Sida spp, Portulaca spp., Richardia spp., Ambrosiaspp., Calandrinia spp., Sisymbrium spp., Sesbania spp., Capsella spp.,Sonchus spp., Euphorbia spp., Helianthus spp., Coronopus spp., Salsolaspp., Abutilon spp., Vicia spp., Epilobium spp., Cardamine spp., Picrisspp., Trifolium spp., Galinsoga spp., Epimedium spp., Marchantia spp.,Solanum spp., Oxalis spp., Metricaria spp., Plantago spp., Tribulusspp., Cenchrus spp. Bidens spp., Veronica spp., and Hypochaeris spp.

Particular examples of dicotyledonous harmful plants species on whichthe herbicidal combinations and compositions according to the presentinvention act efficiently are selected from amongst the speciesAmaranthus spinosus, Polygonum convolvulus, Medicago polymorpha, Mollugoverticillata, Cyclospermum leptophyllum, Stellaria media, Gnaphaliumpurpureum, Taraxacum offscinale, Oenothera laciniata, Amsinckiaintermedia, Erodium cicutarium, Erodium moschatum, Erigeron bonariensis,Senecio vulgaris, Lamium amplexicaule, Erigeron canadensis, Polygonumaviculare, Kochia scoparia, Chenopodium album, Lactuca serriola, Malvaparviflora, Malva neglecta, Ipomoea hederacea, Ipomoea lacunose,Brassica nigra, Sinapis arvensis, Urtica dioica, Amaranthus blitoides,Amaranthus retroflexus, Amaranthus hybridus, Amaranthus lividus, Sidaspinosa, Portulaca oleracea, Richardia scabra, Ambrosia artemisiifolia,Calandrinia caulescens, Sisymbrium irio, Sesbania exaltata, Capsellabursa-pastoris, Sonchus oleraceus, Euphorbia maculate, Helianthusannuus, Coronopus didymus, Salsola tragus, Abutilon theophrasti, Viciabenghalensis L., Epilobium paniculatum, Cardamine spp, Picris echioides,Trifolium spp., Galinsoga spp., Epimedium spp., Marchantia spp., Solanumspp., Oxalis spp., Metricaria matriccarioides, Plantago spp., Tribulusterrestris, Salsola kali, Cenchrus spp., Bidens bipinnata, Veronicaspp., and Hypochaeris radicata.

As shown in the biological examples hereinbelow, for example thefollowing harmful plants or undesired plants are controlled in a moreeffective and superior manner by application of the herbicidalcombinations and compositions according to the present invention whencompared to L-glufosinate alone: Amaranthus retroflexus, Stellariamedia, Lolium multiflorum and Poa annua.

If the herbicide combinations according to the present invention and thecompositions according to the present invention are appliedpost-emergence to the green parts of the plants, growth likewise stopsdrastically a very short time after the treatment and the weed plantsremain at the growth stage of the point of time of application, or theydie completely after a certain time, so that in this manner competitionby the weeds, which is harmful to the crops, is eliminated at a veryearly point in time and in a sustained manner.

The herbicide combinations according to the present invention and thecompositions according to the present invention are characterized by arapidly commencing and long-lasting herbicidal action. As a rule, therainfastness of the active compounds in the herbicide combinationsaccording to the present invention is advantageous. A particularadvantage is that the dosages of the herbicides (i) and (ii) as definedin the context of the present invention can be adjusted to such a lowquantity that their soil action is low. This also allows them to beemployed in sensitive crops (such as (young) plantation crops). Also,the combination of herbicides (i) and (ii) as defined in the context ofthe present invention allows the application rate of the herbicides (i)and (ii) required to be reduced.

In particular when the herbicide combinations as defined in the contextof the present invention and the compositions comprising a herbicidecombination as defined in the context of the present invention areemployed application rates may be reduced, a broader spectrum ofbroad-leaved weeds and grass weeds maybe controlled, the herbicidalaction may take place more rapidly, the duration of action may belonger, the harmful plants may be controlled better while using onlyone, or few, applications, and the application period which is possibleto be extended.

The abovementioned properties and advantages are of benefit for weedcontrol practice to keep agricultural crops free from undesiredcompeting plants and thus to safeguard and/or increase the yields fromthe qualitative and/or quantitative point of view. These novelcombinations markedly exceed the technical state of the art with a viewto the properties described.

Owing to their herbicidal and plant-growth-regulatory properties, thecompositions according to the present invention can be employed forcontrolling harmful plants in genetically modified crops or cropsobtained by mutation/selection. These crops are distinguished as a ruleby particular, advantageous properties, such as resistances toherbicidal compositions or resistances to plant diseases or causativeagents of plant diseases such as particular insects or microorganismssuch as fungi, bacteria or viruses. Other particular properties relate,for example, to the harvested material with regard to quantity, quality,storability, composition and specific constituents. Thus, for example,transgenic plants are known whose starch content is increased or whosestarch quality is altered, or those where the harvested material has adifferent fatty acid composition.

The present invention also relates to a method of controlling undesiredvegetation (e.g. harmful plants), which comprises applying a herbicidecombination and compositions as defined in the context of the presentinvention or applying a composition as defined in the context of thepresent invention, preferably by the post-emergence method, to harmfulor undesired plants, parts of said harmful or undesired plants, or thearea where the harmful or undesired plants grow, for example the areaunder cultivation.

In the context of the present invention “controlling” denotes asignificant reduction of the growth of the harmful plant(s) incomparison to the untreated harmful plants. Preferably, the growth ofthe harmful plant(s) is essentially diminished (60-79%), more preferablythe growth of the harmful plant(s) is largely or fully suppressed(80-100%), and in particular the growth of the harmful plant(s) isalmost fully or fully suppressed (90-100%).

Thus, in a further aspect, the present invention relates to a method for

-   -   controlling undesired plant growth,        and/or    -   controlling harmful plants,        comprising the step of applying a combination of herbicides        according to the present invention (preferably in one of the        preferred embodiments defined herein) or a composition according        to the present invention (preferably in one of the preferred        embodiments defined herein) onto the undesired plants or the        harmful plants, on parts of the undesired plants or the harmful        plants, or on the area where the undesired plants or the harmful        plants grow.

The preferred application rates [indicated as g/ha i.e. grams of activeingredient per hectare] of the herbicides (components (i) and (ii)) usedin the context of the present invention as defined herein are asfollows.

In a preferred method for controlling undesired plant growth and/or forcontrolling harmful plants, the total amount per hectare per Gregoriancalendar year of component (i) L-glufosinate and the agronomicallyacceptable salts thereof does not exceed 1000 g, and preferably does notexceed 900 g.

In many cases it is preferred in the context of a method for controllingundesired plant growth, and/or for controlling harmful plants accordingto the present invention that the total amount per hectare per Gregoriancalendar year of component (i) L-glufosinate and the agronomicallyacceptable salts thereof does not exceed 750 g, more preferably does notexceed 600 g, and even more preferably does not exceed 480 g.

In a preferred method for controlling undesired plant growth and/or forcontrolling harmful plants, the total amount per hectare per Gregoriancalendar year of component (ii) indaziflam does not exceed 30 g, andpreferably does not exceed 25 g.

These lower amounts of component (ii) indaziflam are particularlysuitable to achieve the surprising and desired aspects (c), (d) and/or(e) mentioned above in the context of the present invention.

In a particularly preferred method for controlling undesired plantgrowth and/or for controlling harmful plants, the total amount perhectare per Gregorian calendar year of component (i) L-glufosinate andthe agronomically acceptable salts thereof does not exceed 900 g (andpreferably does not exceed 600 g), and the total amount per hectare perGregorian calendar year of component (ii) indaziflam does not exceed 25g.

In a more particularly preferred method for controlling undesired plantgrowth and/or for controlling harmful plants, the total amount perhectare per Gregorian calendar year of component (i) L-glufosinate andthe agronomically acceptable salts thereof does not exceed 750 g(preferably does not exceed 600 g, and more preferably does not exceed480 g), and the total amount per hectare per Gregorian calendar year ofcomponent (ii) indaziflam does not exceed 24 g.

Preferably, the combinations of herbicides according to the presentinvention as defined herein or the compositions according to the presentinvention as defined herein are applied in a method for controllingundesired plant growth and/or for controlling harmful plants onpermanent crops and/or on permanent crop land. Preferably, the permanentcrops in the context of the present invention are plantation crops, andpreferably are selected from the group consisting fruit crops andorchard crops (preferably fruit trees, citrus trees, mango trees, olivetrees, grape vines, coffee, cocoa, tea, and berries (such asstrawberries, raspberries, blueberries and currants)), Musaceae sp.crops (for example banana or plantain crops), nut trees (preferablyalmond trees, walnut trees, pistachio trees, pecan trees, hazelnuttrees), oil palm trees, rubber trees, sugarcane and cotton. Even morepreferably, the permanent crops in the context of the present inventionare those mentioned above as even more preferred permanent crops,particularly preferably, the permanent crops in the context of thepresent invention are those mentioned above as particularly preferredpermanent crops.

As already mentioned above, the herbicide combinations as defined in thecontext of the present invention can not only be used as mixedformulations, if appropriate together with further agrochemically activecompounds, additives and/or customary formulation auxiliaries, which arethen applied in the customary manner as a dilution with water, but alsoas so-called tank mixes by jointly diluting the separately formulated,or partially separately formulated, components with water.

The herbicide combinations as defined in the context of the presentinvention and the compositions comprising a herbicide combination asdefined in the context of the present invention can be formulated invarious ways, depending on the prevailing biological and/orchemical-physical parameters. The following are examples of generalpossibilities for formulations: wettable powders (WP), water-solubleconcentrates, emulsifiable concentrates (EC), aqueous solutions (SL),emulsions (EW) such as oil-in-water and water-in-oil emulsions,sprayable solutions or emulsions, suspension concentrates (SC), oildispersions (OD), oil- or water-based dispersions, suspoemulsions, dusts(DP), seed-dressing materials, granules for soil application or forbroadcasting, or water-dispersible granules (WG), ULV formulations,microcapsules or waxes.

Herbicidal formulations comprising glufosinate or salts thereof (such asglufosinate-ammonium), are well known in the art, for example, from EP0048436, EP 0336151 A2, U.S. Pat. No. 5,258,358, U.S. Pat. No.5,491,125, US 2005/0266995 A1, US 2005/0266998 A1, US 2005/266999 A1, US2007/0184982 A1 or US 2008/0045415 A1, and such formulations aresuitable in the context of the present invention.

Preferably, the herbicidal combinations according to the presentinvention (preferably in one of the preferred embodiments definedherein) and compositions according to the present invention (preferablyin one of the preferred embodiments defined herein) are used in the formof suspension concentrates (SC), oil dispersions (OD), or microcapsules.

Preferably, the a combination of herbicides according to the presentinvention (preferably in one of the preferred embodiments definedherein) and the compositions according to the present invention(preferably in one of the preferred embodiments defined herein) areeasily and readily obtained, by combining the components (i) and (ii) inthe ratio by weight as defined in the context of the present invention,for example by mixing the appropriate amounts if components (i) and(ii).

Thus, in a further aspect, the present invention relates to a method forproducing a combination of herbicides according to the present invention(preferably in one of the preferred embodiments defined herein) and to amethod of producing the compositions according to the present invention(preferably in one of the preferred embodiments defined herein),comprising the steps of

(a) providing component (i),(b) providing component (ii), and(c) combining component (i) and component (ii),such that a combination of herbicides according to the present invention(preferably in one of the preferred embodiments defined herein) or acomposition according to the present invention (preferably in one of thepreferred embodiments defined herein) is obtained.

The individual formulation types are known in principle and aredescribed for example, in: Winnacker-Küchler, “Chemische Technologie”,Volume 7, C. Hauser Verlag Munich, 4^(th) Edition, 1986; van Valkenburg,“Pesticide Formulations”, Marcel Dekker N.Y., 1973; K. Martens, “SprayDrying Handbook”, 3rd Ed. 1979, G. Goodwin Ltd. London.

The formulation auxiliaries required, such as inert materials,surfactants, solvents and other additives are also known and aredescribed, for example, in Watkins, “Handbook of Insecticide DustDiluents and Carriers”, 2nd Ed., Darland Books, Caldwell N.J.; H. v.Olphen, “Introduction to Clay Colloid Chemistry”; 2nd Ed., J. Wiley &Sons, N.Y. Marsden, “Solvents Guide”, 2nd Ed., Interscience, N.Y. 1950;McCutcheon's, “Detergents and Emulsifiers Annual”, MC Publ. Corp.,Ridgewood N.J.; Sisley and Wood, “Encyclopedia of Surface ActiveAgents”, Chem. Publ. Co. Inc., N.Y. 1964; Schönfeldt,“Grenzflächenaktive Äthylenoxidaddukte” [Surface-active ethylene oxideadducts], Wiss. Verlagsgesellschaft, Stuttgart 1976, Winnacker-Küchler,“Chemische Technologie”, Volume 7, C. Hauser Verlag Munich, 4^(th)Edition 1986.

Based on these formulations, combinations with other agrochemicallyactive substances, such as other herbicides not belonging toconstituents (i) and (ii) as defined in the context of the presentinvention, fungicides or insecticides, and with safeners, fertilizersand/or growth regulators, may also be prepared, for example in the formof a readymix or a tank mix.

Wettable powders (sprayable powders) are products which are uniformlydispersible in water and which, besides the active compound, alsocomprise ionic or nonionic surfactants (wetters, dispersants), forexample polyoxethylated alkylphenols, polyethoxylated fatty alcohols orfatty amines, alkanesulfonates or alkylbenzenesulfonates, sodiumlignosulfonate, sodium 2,2′-dinaphthylmethane-6,6′-disulfonate, sodiumdibutylnaphthalenesulfonate or else sodium oleoylmethyltauride, inaddition to a diluent or inert material.

Emulsifiable concentrates are prepared by dissolving the active compoundin an organic solvent, for example butanol, cyclohexanone,dimethylformamide, xylene or else higher-boiling aromatics orhydrocarbons with addition of one or more ionic or nonionic surfactants(emulsifiers). Examples of emulsifiers which may be used are: calciumsalts of alkylarylsulfonic acids, such as calcium dodecylbenzenesulfonate, or nonionic emulsifiers such as fatty acid polyglycol esters,alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propyleneoxide/ethylene oxide condensates, alkyl polyethers, sorbitan fatty acidesters, polyoxyethylene sorbitan fatty acid esters or polyoxethylenesorbitol esters.

Dusts are obtained by grinding the active compound with finely dividedsolid materials, for example talc, natural clays such as kaolin,bentonite and pyrophyllite, or diatomaceous earth.

Suspension concentrates (SC) can be water- or oil-based. They can beprepared, for example, by wet grinding by means of commerciallyavailable bead mills and, if appropriate, addition of furthersurfactants as they have already been mentioned for example above in thecase of the other formulation types.

Emulsions, for example oil-in-water emulsions (EW), can be prepared forexample by means of stirrers, colloid mills and/or static mixers usingaqueous organic solvents and, if appropriate, further surfactants ashave already been mentioned for example above in the case of the otherformulation types.

Granules can be prepared either by spraying the active compound ontoadsorptive, granulated inert material or by applying active compoundconcentrates to the surface of carriers such as sand, kaolinites orgranulated inert material with the aid of binders, for example polyvinylalcohol, sodium polyacrylate or else mineral oils. Suitable activecompounds may also be granulated in the manner conventionally used forthe production of fertilizer granules, if desired in a mixture withfertilizers. As a rule, water-dispersible granules are prepared bycustomary processes such as spray drying, fluidized-bed granulation,disk granulation, mixing with high-speed mixers and extrusion withoutsolid inert material. Regarding the production of disk granules,fluidized-bed granules, extruder granules and spray granules, see, forexample, the methods in “Spray-Drying Handbook” 3rd ed. 1979, G. GoodwinLtd., London; J. E. Browning, “Agglomeration”, Chemical and Engineering1967, page 147 et seq; “Perry's Chemical Engineer's Handbook”, 5th Ed.,McGraw-Hill, New York 1973, pp. 8-57.

As regards further details on the formulation of crop protectionproducts, see, for example, G. C. Klingmam, “Weed Control as a Science”,John Wiley and Sons, Inc., New York, 1961, pages 81-96 and J. D. Freyer,S. A. Evans, “Weed Control Handbook”, 5th Ed., Blackwell ScientificPublications, Oxford, 1968, pages 101-103.

As a rule, the agrochemical formulations comprise 1 to 95% by weight, ofactive compounds, the following concentrations being customary,depending on the type of formulation:

The active compound concentration in wettable powders is, for example,approximately 10 to 95% by weight, the remainder to 100% by weight beingcomposed of customary formulation constituents. In the case ofemulsifiable concentrates, the active compound concentration may amountto, for example, 5 to 80% by weight. Formulations in the form of dustscomprise, in most cases, 5 to 20% by weight of active compound,sprayable solutions approximately 0.2 to 25% by weight of activecompound. In the case of granules such as dispersible granules, theactive compound content depends partly on whether the active compound ispresent in liquid or solid form and on which granulation auxiliaries andfillers are being used. As a rule, the content amounts to between 10 and90% by weight in the case of the water-dispersible granules.

In addition, the abovementioned active compound formulations maycomprise, if appropriate, the conventional adhesives, wetters,dispersants, emulsifiers, preservatives, antifreeze agents, solvents,fillers, colorants, carriers, antifoams, evaporation inhibitors, pHregulators or viscosity regulators.

The herbicidal action of the herbicide combinations according to thepresent invention can be improved, for example, by surfactants,preferably by wetters from the group of the fatty alcohol polyglycolethers. The fatty alcohol polyglycol ethers preferable contain 10-18carbon atoms in the fatty alcohol radical and 2-20 ethylene oxide unitsin the polyglycol ether moiety. The fatty alcohol polyglycol ethers canbe nonionic or ionic, for example in the form of fatty alcoholpolyglycol ethers sulfates, which can be used, for example, as alkalimetal salts (e.g. sodium salts or potassium salts) or ammonium salts,but also as alkaline earth metal salts such as magnesium salts, such assodium C₁₂/C₁₄-fatty alcohol diglycol ether sulfate (Genapol® LRO,Clariant); see, for example, EP-A-0476555, EP-A-0048436, EP-A-0336151 orU.S. Pat. No. 4,400,196 and also Proc. EWRS Symp. “Factors AffectingHerbicidal Activity and Selectivity”, 227-232 (1988). Nonionic fattyalcohol polyglycol ethers are, for example, (C₁₀-C₁₈)-, preferably(C₁₀-C₁₄)-fatty alkohol polyglycol ethers containing 2-20, preferably3-15, ethylene oxide units (e.g. isotridecyl alcohol polyglycol ether),for example from the Genapol® series, such as Genapol® X-030, Genapol®X-060, Genapol® X-080 or Genapol® X-150 (all from Clariant GmbH).

The present invention furthermore embraces the combination of herbicides(i) and (ii) as defined above with the wetting agents mentioned abovefrom the group of the fatty alcohol polyglycolethers which preferablycontain 10-18 carbon atoms in the fatty alcohol radical and 2-20ethylene oxide units in the polyglycol ether moiety and which can bepresent in nonionic or ionic form (for example as fatty alcoholpolyglycol ether sulfates). Preference is given to C₁₂/C₁₄-fatty alcoholdiglycol ether sulfate sodium (Genapol® LRO, Clariant); and isotridecylalcohol polyglycol ether with 3-15 ethylene oxide units, for examplefrom the Genapol® X series, such as Genapol® X-030, Genapol® X-060,Genapol® X-080 or Genapol® X-150 (all from Clariant GmbH). It isfurthermore known that fatty alcohol polyglycol ethers such as nonionicor ionic fatty alcohol polyglycol ethers (for example fatty alcoholpolyglycol ether sulfates) are also suitable for use as penetrants andactivity enhancers for a number of other herbicides, inter alia also forherbicides from the group of the imidazolinones (see, for example,EP-A-0502014).

Moreover, it is known that fatty alcohol polyglycol ethers such asnonionic or ionic fatty alcohol polyglycol ethers (for example fattyalcohol polyglycol ether sulfates) are also suitable as penetrants andsynergists for a number of other herbicides, inter alia also herbicidesfrom the group of the imidazolinones; (see, for example, EP-A-0502014).

The herbicidal effect of the herbicide combinations according to thepresent invention can also be increased using vegetable oils. The termvegetable oils is to be understood as meaning oils from oil-plantspecies, such as soya oil, rapeseed oil, corn oil, sunflower oil,cottonseed oil, linseed oil, coconut oil, palm oil, safflower oil orcastor oil, in particular rapeseed oil, and their transesterificationproducts, for example alkyl esters, such as rapeseed oil methyl ester orrapeseed oil ethyl ester.

The vegetable oils are preferably esters of C₁₀-C₂₂-, preferablyC₁₂-C₂₀-fatty acids. The C₁₀-C₂₂-fatty acid esters are, for example,esters of unsaturated or saturated C₁₀-C₂₂-fatty acids, in particularthose with an even number of carbon atoms, for example erucic acid,lauric acid, palmitic acid and, in particular, C₁₈-fatty acids such asstearic acid, oleic acid, linoleic acid or linolenic acid.

Preferred C₁-C₂₀-alkyl-C₁₀-C₂₂-fatty acid esters are the methyl, ethyl,propyl, butyl, 2-ethylhexyl and dodecyl esters. Preferred glycol- andglycerol-C₁₀-C₂₂-fatty acid esters are the uniform or mixed glycolesters and glycerol esters of C₁₀-C₂₂-fatty acids, in particular thosefatty acids which have an even number of carbon atoms, for exampleerucic acid, lauric acid, palmitic acid and, in particular, C₁₈-fattyacids such as stearic acid, oleic acid, linolic acid or linolenic acid.

The vegetable oils can be present in the herbicidal compositionsaccording to the present invention for example in the form ofcommercially available oil-containing formulation additives, inparticular those based on rapeseed oil such as Hasten′ (VictorianChemical Company, Australia, hereinbelow termed Hasten, mainconstituent: rapeseed oil ethyl ester), Actirob®B (Novance, France,hereinbelow termed ActirobB, main constituent: rapeseed oil methylester), Rako-Binol® (Bayer AG, Germany, termed Rako-Binol hereinbelow,main constituent: rapeseed oil), Renol® (Stefes, Germany, termed Renolhereinbelow, vegetable oil constituent: rapeseed oil methyl ester), orStefes Mero® (Stefes, Germany, hereinbelow termed Mero, mainconstituent: rapeseed oil methyl ester).

In a further embodiment, the present invention embraces the combinationof a herbicide combination as defined in the context of the presentinvention with the vegetable oils mentioned above. Thus, in a furtherembodiment, the present invention embraces the use of compositionscomprising a herbicide combination as defined in the context of thepresent invention comprising the vegetable oils mentioned above, such asrapeseed oil, preferably in the form of commercially availableoil-containing formulation additives, in particular those based onrapeseed oil such as Hasten® (Victorian Chemical Company, Australia,hereinbelow termed Hasten, main constituent: rapeseed oil ethyl ester),Actirob®B (Novance, France, hereinbelow termed ActirobB, mainconstituent: rapeseed oil methyl ester), Rako-Binol® (Bayer AG, Germany,termed Rako-Binol hereinbelow, main constituent: rapeseed oil), Renol®(Stefes, Germany, termed Renol hereinbelow, vegetable oil constituent:rapeseed oil methyl ester), or Stefes Mero® (Stefes, Germany,hereinbelow termed Mero, main constituent: rapeseed oil methyl ester).

For use, the formulations, which are present in commercially availableform, are optionally diluted in the customary manner, for example usingwater in the case of wettable powders, emulsifiable concentrates,dispersions and water-dispersible granules. Preparations in the form ofdusts, soil granules, granules for broadcasting and sprayable solutionsare usually not diluted further with other inert substances prior touse.

A herbicide combination according to the present invention and acomposition comprising the herbicide combination as defined in thecontext of the present invention are preferably applied to the harmfulplants or undesired plants or parts thereof, seeds of the plants or thearea under cultivation (soil of a field), preferably to the green of theharmful plants or parts thereof, or to the green parts of the undesiredplants or parts thereof.

A composition comprising a herbicide combination used in the context ofthe present invention has the advantage of being easier to apply sincethe quantities of the components are already presented in the correctratio to each other. Moreover, the adjuvants in the formulation can bematched optimally to each other.

As already described in more detail above, the present invention furtherrelates to the use of combination of herbicides according to the presentinvention (preferably in one of the preferred embodiments definedherein) or a composition according to the present invention (preferablyin one of the preferred embodiments defined herein) in the field ofagriculture, in particular as plant growth regulators and/or forcontrolling harmful plants or undesired plant growth.

EXAMPLES 1. Products Used

The following products were used in the biological trials describedhereinafter:

Product P1 contained L-glufosinate (i.e. in enantiomeric pure form), notin accordance with the present invention.

Product P2 contained L-glufosinate (i.e. in enantiomeric pure form) andindaziflam [the ratio by weight of the (1*R)-1-fluoroethyldiastereoisomer of indaziflam to the ratio by weight of the(1*S)-1-fluoroethyl diastereoisomer of indaziflam was about 95:5],wherein the ratio by weight of the total amount of L-glufosinate to thetotal amount of indaziflam was 18.75:1.

Product P3 contained L-glufosinate (i.e. in enantiomeric pure form) andindaziflam [the ratio by weight of the (1*R)-1-fluoroethyldiastereoisomer of indaziflam to the ratio by weight of the(1*S)-1-fluoroethyl diastereoisomer of indaziflam was about 95:5],wherein the ratio by weight of the total amount of L-glufosinate to thetotal amount of indaziflam was 37.5:1.

It is known that indaziflam shows insufficient post-emergence efficacyon monocotyledonous and dicotyledonous harmful plant species.Correspondingly, a product containing 4 g/L of indaziflam [the ratio byweight of the (1*R)-1-fluoroethyl diastereoisomer of indaziflam to theratio by weight of the (1*S)-1-fluoroethyl diastereoisomer of indaziflamwas about 95:5] applied in a dose rate of 12 g/ha showed only verylimited post-emergence efficacy on monocotyledonous and dicotyledonousharmful plant species, if any.

2. Biological Trials

In separate pots, biological trials were conducted in the greenhouseunder identical conditions (apart from the treatment with the differentproducts P1, P2 and P3 mentioned above). Each pot contained the samesoil and the same amount of seeds of each of the following weeds (twomonocotyledonous and two dicotyledonous harmful plant species (weedspecies)):

Weed species Code Scientific Name AMARE Amaranthus retroflexus STEMEStellaria media LOLMU Lolium multiflorum POAAN Poa annua

Tables 1 to 6 reflect the respective observed herbicidal activityratings after treatment of the monocotyledonous harmful plant species(BBCH growth stage 11) and dicotyledonous harmful plant species (BBCHgrowth stage 10) for the different products applied once inpost-emergence. The Tables 1 to 6 reflect the observations after certainperiods of time, indicated in days (referred to as DAA=days afterapplication) after start of treatment with/application of the respectiveproduct P1, P2 or P3 mentioned above, each in the amounts indicatedbelow. For example, DAA X refers to the time of X days after applicationof the respective product, and the Tables below reflect the herbicidalactivity observed at that time.

The ratings of the herbicidal activity were performed on a scale of0-100%, wherein 100% activity means that all weed plants had died in therespective pots, 50% herbicidal activity means that the weed coverage inthe respective pots has been reduced by 50% in comparison to theuntreated control pots, and 0% activity means that no herbicidalactivity was observed in the respective pots in comparison to theuntreated control pots.

TABLE 1 Ratings of herbicidal activity against the above-mentionedharmful plant species after a single post-emergence treatment withproduct P1 in an amount of 225 g/ha of L-glufosinate Weed DAA 4 DAA 7DAA 11 DAA 16 STEME 50% 55% 55% 40% LOLMU 15% 10%  5%  5% POOAN 15% 20%20% 15%

TABLE 2 Ratings of herbicidal activity against the above-mentionedharmful plant species after a single post-emergence treatment withproduct P2 in an amount of 225 g/ha of L-glufosinate and 12 g/haindaziflam Weed DAA 4 DAA 7 DAA 11 DAA 16 STEME 55% 98% 100%  100% LOLMU 35% 60% 75% 75% POOAN 20% 30% 40% 50%

TABLE 3 Ratings of herbicidal activity against the above-mentionedharmful plant species after a single post-emergence treatment withproduct P1 in an amount of 375 g/ha of L-glufosinate Weed DAA 4 DAA 7DAA 11 DAA1 6 STEME 70% 60% 55% 35% LOLMU 20% 20% 20% 15% POOAN 25% 30%30% 25%

TABLE 4 Ratings of herbicidal activity against the above-mentionedharmful plant species after a single post-emergence treatment withproduct P2 in an amount of 375 g/ha of L-glufosinate and 20 g/haindaziflam Weed DAA 4 DAA 7 DAA 11 DAA 16 STEME 75% 98% 100%  100% LOLMU 35% 55% 75% 80% POOAN 25% 45% 45% 50%

TABLE 5 Ratings of herbicidal activity against the above-mentionedharmful plant species after a single post-emergence treatment withproduct P1 in an amount of 450 g/ha of L-glufosinate Weed DAA 5 DAA 7DAA 9 DAA 12 AMARE 80% 85% 90% 98% STEME 60% 80% 85% 90% LOLMU 10% 10%10% 10%

TABLE 6 Ratings of herbicidal activity against the above-mentionedharmful plant species after a single post-emergence treatment withproduct P3 in an amount of 450 g/ha of L-glufosinate and 12 g/haindaziflam Weed DAA 5 DAA 7 DAA 9 DAA 12 AMARE 85% 90% 95% 98% STEME 75%90% 95% 98% LOLMU 15% 20% 20% 25%

Table 7 reflects the post-emergence efficacy of indaziflam [the ratio byweight of the (1*R)-1-fluoroethyl diastereoisomer of indaziflam to theratio by weight of the (1*S)-1-fluoroethyl diastereoisomer of indaziflamwas about 95:5] on the above mentioned weeds AMARE, STEME, LOLMU andPOOAN, each at BBCH growth stage 11-12. Indaziflam was used in an amountof 12 g/ha.

TABLE 7 Ratings of herbicidal activity against the above-mentionedharmful plant species after a single post-emergence treatment in anamount of 12 g/ha of indaziflam Weed Regrowth AMARE very weak herbicidaleffect starting on day 7 after treatment STEME no herbicidal effectLOLMU no herbicidal effect POAAN no herbicidal effect

1. Combination of herbicides comprising (i) L-glufosinate and/or one ormore agronomically acceptable salts thereof, and (ii) indaziflam,wherein the ratio by weight of the total amount of component (i) to thetotal amount of component (ii) is equal to or greater than 10:1. 2.Combination of herbicides according to claim 1, wherein the ratio byweight of the total amount of component (i) to the total amount ofcomponent (ii) in the combination of herbicides is in the range of from10:1 to 35:1.
 3. Combination of herbicides according to claim 1, whereinthe ratio by weight of the total amount of component (i) to the totalamount of component (ii) in the combination of herbicides is in therange of from 12:1 to 30:1.
 4. Combination of herbicides according toclaim 1, wherein the ratio by weight of the total amount of component(i) to the total amount of component (ii) in the combination ofherbicides is in the range of from 15:1 to 25:1.
 5. Compositioncomprising a combination of herbicides as defined in claim
 1. 6.Composition according to claim 5, wherein the total amount of component(i) is equal to or less than 600 g/L, optionally the total amount ofcomponent (i) is equal to or less than 450 g/L, optionally the totalamount of component (i) is equal to or less than 300 g/L, in each casebased on the total amount of the composition.
 7. Composition accordingto claim 5, wherein the total amount of component (ii) is in the rangeof from 2 to 20 g/L, optionally in the range of from 3 to 15 g/L,optionally in the range of from 3 to 12 g/L, optionally in the range offrom 3 to 10 g/L, optionally in the range of from 3 to 6 g/L, in eachcase based on the total amount of the composition.
 8. Compositionaccording to claim 5, wherein the total amount of component (i) is inthe range of from 125 to 300 g/L, optionally in the range of from 125 to250 g/L, and the total amount of component (ii) is in the range of from3 to 10 g/L, optionally in the range of from 3 to 6 g/L, in each casebased on the total amount of the composition.
 9. Composition accordingto claim 5, wherein the composition additionally comprises one or morefurther components selected from the group consisting of formulationauxiliaries, additives customary in crop protection, and furtheragrochemically active compounds.
 10. Composition according to claim 5,wherein the composition in the form of a suspension concentrate (SC),oil dispersion (OD), or in form of microcapsules.
 11. Method forproducing a combination of herbicides as defined in claim 1 or acomposition thereof, comprising (a) providing component (i), (b)providing component (ii), and (c) combining component (i) and component(ii), such that a combination of herbicides or a composition thereof isobtained.
 12. Method for controlling undesired plant growth, and/orcontrolling harmful plants, comprising applying a combination ofherbicides as defined in claim 1 or a composition thereof onto theundesired plants or the harmful plants, on parts of the undesired plantsor the harmful plants, or on an area where the undesired plants or theharmful plants grow.
 13. Method according to claim 12, wherein the totalamount per hectare per Gregorian calendar year of component (i)L-glufosinate and the agronomically acceptable salts thereof does notexceed 1000 g, and optionally does not exceed 750 g.
 14. Methodaccording to claim 12, wherein the total amount per hectare perGregorian calendar year of component (ii) indaziflam does not exceed 30g, and optionally does not exceed 25 g.
 15. A product comprising acombination of herbicides as defined in claim 1 or a composition thereofin the field of agriculture.